Process for preparing an alpha-substituted acrylate

Abstract

The present disclosure relates to a process for preparing an alpha-substituted acrylate, the process comprising: a) combining starting materials comprising an alpha-(halomethyl) acrylate and an organozinc compound, thereby forming a product comprising the alpha-substituted acrylate.

What is claimed is: 
     
         1 . A process for preparing an alpha-substituted acrylate, the process comprising:
 a) combining starting materials comprising an alpha-(halomethyl) acrylate and an organozinc compound of the formula R 2 Zn,   thereby forming a product comprising the alpha-substituted acrylate, wherein:   the alpha-substituted acrylate has the formula (I):   
       
         
           
           
               
               
           
         
         the alpha-(halomethyl) acrylate has the formula (II): 
       
       
         
           
           
               
               
           
         
         each R independently is a C1-C26 hydrocarbyl group or a polyolefinyl group; 
         each R1 independently is a C1-C30 hydrocarbyl group; and 
         X is a halogen. 
       
     
     
         2 . The process of  claim 1 , wherein the starting materials of step a) further comprise a solvent. 
     
     
         3 . The process of  claim 2 , wherein the solvent is a non-aromatic hydrocarbon solvent. 
     
     
         4 . The process of  claim 1 , wherein the process excludes any transmetallation step or reaction. 
     
     
         5 . The process of  claim 1 , wherein the starting materials of step a) further comprise an organocatalyst. 
     
     
         6 . The process of  claim 1 , wherein each R independently is a C1-C26 hydrocarbyl group. 
     
     
         7 . The process of  claim 1 , where each R independently is a polyolefinyl group, which can be defined by the properties of R—H, wherein R—H has a number average molecular weight of greater than 365 g/mol. 
     
     
         8 . The process of  claim 7 , wherein the polyolefinyl group is an ethylene-based polymeryl group. 
     
     
         9 . The process of  claim 8 , wherein the polyolefinyl group is an ethylene homopolymeryl group comprising units derived from ethylene. 
     
     
         10 . The process of  claim 8 , wherein the polyolefinyl group is an ethylene/alpha-olefin interpolymeryl group comprising units derived from ethylene and a C3-C30 alpha-olefin. 
     
     
         11 . The process of  claim 7 , wherein the polyolefinyl group is a propylene-based polymeryl group. 
     
     
         12 . The process of  claim 11 , wherein the polyolefinyl group is a propylene homopolymeryl group comprising units derived from propylene. 
     
     
         13 . The process of embodiment 11, wherein the polyolefinyl group is a propylene/alpha-olefin interpolymeryl group comprising units derived from propylene and either ethylene or a C4-C30 alpha-olefin.